Dog Sitting Crestwood
Book a Crestwood dog sitter to watch your dog in your sitter’s home or yours.
Over 137 pet parents in Crestwood have booked dog sitting
Crestwood, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Huge thanks to this amazing duo! They stepped in for a last-minute booking and were so friendly, attentive, and thorough with their questions. Piper and Ava instantly loved them and soaked up all the attention. We’ll definitely rebook in the future!”
About: I have owned and fostered dogs and cats for as long as I can remember. I have experience with puppies, small, medium and large dogs. I have a great time interacting with and entertaining fur babies! I am currently on summer break from school, so most weeks my schedule is pretty open for the summer. I am typically available weekend and week days. I have experience walking small, medium, and large dogs. I have handled high and low energy dogs and cats. I walk my own dogs daily and have cared for high energy pups in the neighborhood.
“Katie was an amazing cat sitter! She took excellent care of our cat and made him feel loved and cared for while we were gone on our trip. I highly recommend Katie for all your pet sitting needs and we will definitely be rebooking Katie for our future pet sitting needs! Thank you, for taking such great care of our furry boy!”
“Alicia took great care of my cats when I was out of town! She was punctual, respectful, and communicated well from the moment I sent the booking request. I came home to happy cats, highly recommended!”
About: I am a traveler who wants to spend weeks home with your pet!! I have owned dogs of all ages and know how to speak the language! Woof! 20 years of pet sitting experience from family pets as a teen, having my own old boy in my 20s, to helping family and friends with their babies now! I make my own schedule so I am highly available when I am not traveling! Very flexible. Always honest about my availability and what I am able to provide. I am very good at reading what a dog needs and not lazy about it. Walk at 5 am? On it. Weird feeding times? Not a problem.
“Ryan is a breath of fresh air after having several poor pet sitter experiences. We are very thankful to have found her, as we are completely at ease during our trips out of town. She is thoughtful, prompt, and thorough. We love her and so do Bonnie and Panda!”
About: Hello! I am 19 years old and currently attend college. I have many years of pet care experience of various different animals since I was in elementary school. I enjoy hanging out and taking care of pets more than anything and I’d love to make sure your animals get genuine care that leaves them with the ability to live a long, happy, and healthy life! When I am home from college during spring break, summer, and winter break, my schedule is moderately flexible. I am able to fit in pet care whenever and have plenty of time to play with and take care of my cats and dogs every day. When I am at your home I will make sure it is a safe environment for the animals and that there is nothing they can be harmed by. I love going on walks at any time of the day as well as playing with the dogs or cats with toys, we can even work on some simple training together! Your pet will be safe, comfortable, happy, and healthy when they are in my care. :)
About: I have had pets and taken care of other's pets for most of my life! I absolutely adore animals of all kinds. I have been house/pet sitting for the last few years on my own but I'm trying to expand my client base and meet new furry friends! I also have lots of experience with cats! A large portion of my clients prefer overnight stays but I am willing to do drop ins as well. I'd love to hear from you soon. I currently work part time and my schedule is pretty flexible. With notice I can make sure I am able to spend plenty of time with your babies! I have done some house sitting before and never had any complaints! I am also very responsive and I will take good care of your pets and your home. No worries!
“Kelly looked after our two kitties again and did a great job! She was very communicative, spent a lot of time playing with them to make them feel comfortable, and sent a lot of really good pictures to keep us updated. Would definitely recommend.”
About: With a lifelong passion for animals and two cherished dogs of my own, I bring extensive pet care experience to every interaction. From walks to playtime, I will prioritize your pets well-being and happiness above all else! I believe that one of the core principles to being an above average pet sitter is not only loving care, but mental stimulation through games and activities! Having cared for my own dogs into their elderly years, I’m now animal first aid certified and comfortable with all stages of life. I’m a college student with about 4 hours of free time in the middle of the day between my morning class and afternoon class. I’m available to hang out with your furry friend between my classes usually and all evenings, so long as I’m able to also get my work done! I can provide daily walks, play time and snuggles for your pet! When entrusted with the care of pets in clients’ homes, I prioritize creating a comfortable and nurturing environment for the animals. I closely follow the instructions provided by pet parents regarding feeding schedules, exercise, and any special needs. I ensure a clean and hygienic living environment through cleaning up accidents, regular potty breaks depending on your dog’s size (smaller dogs usually need to go more frequently) and litter box cleaning. Beyond the basic care, I try to engage pets through playtime, walks and even just companionship. It’s important to maintain their mental and emotional well-being in their owner’s absence. I also regularly update and communicate with clients to reassure them that their beloved companion is in caring and capable hands.
“Katie took wonderful care of our two dogs, making sure they had ample breaks during the day, sticking to their schedule and going above and beyond to make sure the pups were comfortable while we were gone. A+ all around, thank you Katie!!!”
About: Hi, I’m Julia! With 6+ years of pet care experience—including two years at a dog daycare and training my own dog from puppyhood—I’m comfortable caring for puppies, seniors, anxious dogs, and any dog in between. I’m certified in both Pet CPR and Pet First Aid, and I will always tailor my care to your dog’s personality and routine. Whether that means stopping to smell every tree on a walk, respecting their space, or playing fetch until they’re happily worn out, your dog’s comfort comes first. Photo updates (and pup cups) are always included! I work part-time (often in the evenings) and have a flexible schedule with several days off per week, giving me plenty of time for walks, drop-in visits, and daytime care! My schedule allows me to be consistent and reliable for your pup. I’m currently fully booked for overnight stays and boarding through the rest of the summer, but I’m happy to help with daytime services in the meantime. I step into your dog’s routine so they feel comfortable and secure when I’m around. I provide calm, in-home care that matches their energy. We’ll play if they’re feeling active, take it slow when they’re not—I will always follow their comfort level! During overnight stays, I stick closely to your pup’s routine and make sure they’re comfortable throughout my visit. I always clean and tidy before leaving, so you come home to both a well cared-for space and dog. *Please note, I provide house sitting for non-smoking homes only.
“Claire was incredible! Couldn’t recommend her enough. We didn’t worry about our dog at all when we were out of town because of Claire’s extremely thorough check ins + pictures. She’s extremely personable and our dog loved her!”
“Emily was fantastic! We have 1 very reactive dog so it is a bit of a challenge to get her acclimated to new people. Emily had such a calming presence and was so patient with our dog. She communicated very well and followed all instructions. We have already booked Emily for more trips and visits.”
About: I have been a cat mom for 6 years and a dog mom of 2 years. I have two cats, one with a special diet, and two dogs, both with special needs of their own. I am very accustomed to taking care of fur babies of all shapes and sizes, with different needs and /personal preferences/ (my Lisa will not go number 2 without a walk and a treat lol). I do not discriminate when it comes to pets and am looking forward to meeting yours! I work varying hours throughout the week but have a 40 hour week schedule and I am always off on Saturdays and Sundays. I can be available in the mornings some days but will primarily be available in the evenings. I have a fenced yard and two friendly dogs and two friendly cats and a husband who is another animal lover like myself. I have rooms that can have doors shut if needed for space. I am used to easing animals into getting to know one another with treats and smells.
“Misty was great with our Germans. We did a meet and greet a few days before and they were so calm around her and she did great with them while I was out of town. I would definitely recommend her to anyone. Thanks Misty!”
The median cost per visit for dog sitting in Crestwood is $20
Dog parents share their Rover experiences - Crestwood
Nicole did a fabulous dog with our 2 pugs. She is meticulous and shows up on time, every time. Our one pug can be very finicky and does not like to walk. But Nicole is patient and gentle. She always follows my instructions. The dogs love her. I would highly recommend her. She did drop in visits to let the dogs out of their crates, when I was gone from home 8 hours. She also sat outside, under their favorite tree, and let them observe their world.
Sarah was a wonderful dog sitter for our two older large dogs. She is warm & caring. Sarah was prompt on her visits & sent great pictures of our dogs. We felt very relieved to know that they were being so well taken care of. We will definitely use her to watch them in the future!
This was my first time using Rover to have someone check on my dogs. I was a bit nervous of how it would go since my dogs get scared easily of new people, but Karen was very patient and attentive with them and overall did a fantastic job! She provided updates during each of the check ins and bonded with the dogs as the days went by. I would 100% recommend Karen as a dog sitter and if I need someone to watch my dogs again using Rover, Karen would be my first choice!
Anne was absolutely wonderful with our four month old puppy. He loves meeting new people, but is still very energetic (and teething). She was very patient with him and added in lots of playtime to tire him out. We will be highly recommending her to friends and family in the area!
Emily was so trustworthy and kind!! She took such great care of our two dogs on short notice, making sure to give them plenty of love, walks, playtime, and following our complicated pill and feeding routine. We have never felt so comfortable leaving town and will definitely ask for her help again in the future!
E was fantastic in taking care of my high maintenance pup! She was friendly, communicative, punctual, diligent, and followed the exact care instructions provided. My dog is a high flight risk and my booking was somewhat last minute, but none of that was an issue and she was professional throughout. I will definitely be booking her next time I need a drop-in or pet sitter!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog sitting - Crestwood
Select a filter and find qualifying sitters offering dog sitting.Sitters in Crestwood average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Crestwood
Frequently asked questions about Rover
The average cost for Dog Sitting in Crestwood on Rover is $23.43 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of August 2026, there are 2,697 sitters on Rover offering Dog Sitting across Crestwood. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Crestwood stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Crestwood choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Crestwood with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Crestwood. On Rover:
- 94% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 94% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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